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Non-Palladium-Catalyzed Approach to the Synthesis of Oxindoles

Molecules (Basel, Switzerland), 2022-08, Vol.27 (16) [Peer Reviewed Journal]

COPYRIGHT 2022 MDPI AG ;ISSN: 1420-3049 ;EISSN: 1420-3049 ;DOI: 10.3390/molecules27165304

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  • Title:
    Non-Palladium-Catalyzed Approach to the Synthesis of Oxindoles
  • Author: Koo, Jahyun ; Kim, Minsu ; Shin, Kye Jung ; Seo, Jae Hong
  • Subjects: Methods ; Palladium ; Palladium catalysts
  • Is Part Of: Molecules (Basel, Switzerland), 2022-08, Vol.27 (16)
  • Description: Two novel synthetic approaches for synthesizing (E)-3-(1,3-diarylallylidene)oxindoles from oxindole were developed. All previously reported methods for synthesizing 3-(1,3-diarylallylidene)oxindoles utilized palladium-catalyzed reactions as a key step to form this unique skeleton. Despite high efficiency, palladium-catalyzed reactions have limitations in terms of substrate scope. Especially, an iodoaryl moiety cannot be introduced by the previous methods due to its high reactivity toward the palladium catalyst. Our Knoevenagel/allylic oxidation/Wittig and Knoevenagel/aldol/dehydration strategies complement each other and show broad substrate scope, including substrates with iodoaryl groups. The current methods utilized acetophenones, benzylidene phosphonium ylides, and benzaldehydes that are commercially available or easily accessible. Thus, the current synthetic approaches to (E)-3-(1,3-diarylallyldiene)oxindoles are readily amendable for variety of oxindole derivatives.
  • Publisher: MDPI AG
  • Language: English
  • Identifier: ISSN: 1420-3049
    EISSN: 1420-3049
    DOI: 10.3390/molecules27165304
  • Source: GFMER Free Medical Journals
    PubMed Central
    Alma/SFX Local Collection
    ProQuest Central
    DOAJ Directory of Open Access Journals
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